Ethanolamine → HCID 12698195, compound

HRID 1180623Notes

Reaction equation

HRID 1180623 reaction equation
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[C:13]([C:14]([OH:16])=O)=[CH:12][C:11]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:10]([Cl:21])[CH:9]=2)[O:4][CH:5]=1.CCN=C=NCCCN(C)C.[CH2:33]([CH2:35][NH2:36])[OH:34]>CN(C=O)C.ClCCl>[Cl:21][C:10]1[CH:9]=[C:8]([NH:7][CH2:6][C:3]2[O:4][CH:5]=[CH:1][CH:2]=2)[C:13]([C:14]([NH:36][CH2:35][CH2:33][OH:34])=[O:16])=[CH:12][C:11]=1[S:17](=[O:19])(=[O:18])[NH2:20]

Participants

6

Reactant 3

HCID 700EthanolamineHCID 3440FurosemideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

Product 1

HCID 12698195HCID 12698195, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To furosemide (1.013 g, 3.0627 mmol) in DMF (3 mL) was added EDAC (608.3 mg, 3.173 mmol) in dichloromethane (3 mL) and then ethanolamine (185 μL, 3.065 mmol). The reaction solution was stirred at ambient temperature for 3 hours, and concentrated to dryness under high vacuum. The crude product was treated with water, and the resultant gum collected and chromatographed on silica gel eluting with methanol:dichloromethane (1:20) to give the title compound (476 mg, 42% yield). Mp 183-185° C. 1H NMR (300 MHz, CD3OD) δ8.17 (s, 1H), 7.45 (m, 1H), 6.94 (s, 1H), 6.37-6.36 (m, 1 H), 6.32-6.31 (m, 1H), 4.44 (s, 2H), 3.70-3.66 (m, 2H), 3.32-3.29 (m, 2H). 13C NMR (75 MHz, CD3OD) δ 170.4, 153.0, 152.7, 143.6, 136.7, 131.3, 127.5, 114.8, 114.4, 111.4, 108.5, 61.5, 43.2, 40.7. LRMS (APIMS) m/z 374(MH+).

Workup

  1. concentrationconcentrated to dryness under high vacuum
  2. additionThe crude product was treated with water
  3. customthe resultant gum collected
  4. customchromatographed on silica gel eluting with methanol:dichloromethane (1:20)

Sources & evidence

ORD record
ord-fcc36622f4694e329545eab23952b259
Source dataset
uspto-grants-2007_10
Patent number
US07282519B2

Reaction notes

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